Winky Has an Adventure

I thought it would be fun to write a little story from a slightly different perspective. Sorry about all the dick pics. Enjoy!

Winky looks nervous. We are on the way home to get a spanking and the little fella isn’t very happy. He probably doesn’t like being all exposed but the rule is “naughty little boys don’t get pants until after spankees are all done.” 


When we found out that she knew we had been naughty, he got all big and hard (he’s a grower and clearly not a show’er). But then we got naked and started driving and he got super shy. 

I don’t know why he isn’t excited; It won’t be too long before he will get to make squirties just like a big penis. She’ll put down a towel under my pee-pee and if I concentrate super hard during my spanking and wiggle just right, the white sticky stuff will squirt out and for a couple seconds, the spanking won’t hurt at all! Afterward, though, it will hurt real bad and Winky will get even smaller than in the picture. She spanks with the hairbrush after Winky makes squirties because she says it is super extra naughty when the squirts happen. She hates it when I make my messes and I get extra spanks if any of it gets on her.

I hope he squirts out a big puddle today. The big ones usually feel really good. She sounded mad on the phone though like she is going to give me lots of spanking before I get to wiggle on the towel and probably a lot after my pee-pee makes his messy too.

I don’t like spankee time ‘cause it hurts my bottom but I really don’t like it when she makes me do squirties first or before most of my punishment. When my pee-pee is hard and full, she knows that hurts less than after he’s empty and soft again. Winky likes to wait too, I think; he always makes bigger puddles when I get most of my spanks before I do wiggles.

I have to put my towel under Winky before every spanking in case I have an accident or leak. He leaks sometimes like he is crying too.

She was mad at me for not shaving so I am getting extra spanks for having stubble when I got home. I had to get in the shower, shave, and then get some spanking on my wet bottom. That hurts real bad. She says that I am going to have more extra spanks later too.

She’s pretty mad because Winky made a mess in my pajamas while I was sleeping. I tried to tell her that it wasn’t my fault but that just made her angrier.

He sure gets hard during my spankings! Sometimes I even think my sticky stuff is about to squirt out.

For this spanking, I had to kneel next to the ottoman. She was using the paddle that makes both my cheeks bounce, jiggle, sting, and burn at the same time. Winky seems to like the paddle cause he gets super hard but I can almost never make squirties when he doesn’t touch anything. I still wiggle a lot but even though he is so hard and ready to make, he just bobs in the air right over my towel.

When he is all hard like this, it is like Winky thinks he is just like those big penises that get to have sexy time with girls. I don’t get to do that. She says that because my Winky is just a small pee-pee that squirts too quickly, he wouldn’t be able to make a girl feel good.

He makes a lot of the yummy slippery drips like he wants to be ready in case she changes her mind. Or maybe they are tears because he is so sad and frustrated. He wants it so bad and she won’t even touch him.

I’ve had a bunch of spankings and my bottom really hurts. She let me keep my squirts inside for all the spankings so far. I’ve been crying a little and little Winky leaked all over my towel and my legs too.

It is time to make squirties so I got to put my towel down on the bed and now when I get this next spanking, I might be able to wiggle a little. If I do it just right and concentrate really hard, Winky will tingle and I’ll be able to make my squirts.

She has the hairbrush. I’m scared of the hairbrush. My bottom is already very ouchy and the hairbrush is super ouchy too.

Winky made a messy! The spanks weren’t very hard while I was wiggling and so it wasn’t too hard to make. As soon as the squirts started though, I think she started spanking a lot harder. She didn’t stop until I was begging and crying.

She let me take a picture but I’m going to get my extra spanks now. I hate extra spanks.

Owwiee!! My bottom is on fire! My little winky got super small again now that he made a messy. The sticky stuff is all over my tummy too (but I didn’t take a picture of that). He didn’t make a big puddle today; I think he’s shy ‘cause of the camera. The tingles felt good though and it always feels good when he makes the squirts even if they are little ones like today.

It makes me sad that Winky gets me in trouble so that I have to have spankees. I wish he was a big penis so that we could make our squirts into a woman. He makes me dream about doing sex things that I’m not allowed to do.

I like being little again. I don’t think about sexy things when Winky is soft. For a day or two, I won’t think as much about naughty things. If I do, my ouchy bottom will remind we to think of something else!

I’ll be good today, but tomorrow the bad thoughts will start again and the day after, well, I probably won’t be able to think about anything else. In just a couple days, Winky won’t be able to stay small again and if she catches me big and hard or he makes naughty in my pajamas or if I am super naughty and play with Winky even a little bit, it will be spankee time again. I hope my bottom feels better by then.

Thanks for reading about Winky’s adventure!